Cyclohexene oxide → 2-(But-3-en-1-yloxy)cyclohexanol
Reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[CH2:8]([OH:12])[CH2:9][CH:10]=[CH2:11]>>[CH2:8]([O:12][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[OH:7])[CH2:9][CH:10]=[CH2:11]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of cyclohexene oxide (3-1) (10.0 g, 102 mmol) in 3-buten-1-ol (17.4 mL, 204 mmol) cooled to 0° C. was added FeCl3 (1.65 g, 10.2 mol) The mixture was removed from the ice bath and stirred at rt for 1 hr. The reaction was quenched with water and extracted ether. The combined organics were washed with brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.00-5.15 (m, 2H), 3.69-3.76 (m, 1H), 3.39-3.44 (m, 2H), 2.98-3.05 (m, 1H), 2.74 (s, 1H), 2.30-2.39 (m, 2H), 1.94-2.11 (m, 3H), 1.61-1.79 (m, 3H), 1.06-1.37 (m, 2H).